My father-in-law constantly gave money (over $400k) to his son (my brother-in-law) over the years. My brother-in-law would always get in trouble ($$ wise). b-in-law & his DW (she probably was the biggest spender) spent like there was no tomorrow. They constantly boasted about their expensive vacations, cars, clothes, and eating out every night.
A couple of years ago, just as the housing market was crashing, b-in-law and his DW wanted f-in-law's last $100k of savings to buy a lot and build house to sell for profit (he's a builder). My father-in-law came to us and asked if we needed any money and we said no you should hold on to it (in case he would need it). He also asked my DW's 2 other siblings if they needed money and they also told him to hang on to it. He was getting older and had some health issues and might need it for his care, it was his last savings but he did have a pension that covered his expenses. My brother-in-law took all the money. My father-in-law told the siblings that they would get 1/3 each once b-in-law was done with the $100k. I told my DW we should have kept the money he offered, and put it away for f-in-law, the 2 other siblings said the same thing.
I had told b-in-law not to buy a lot since the market was slowing, prices had just doubled & could not go up any more and rates were going up etc, that they should wait for a better deal in a couple of years. b-in-law said it was different where he lived, that he should be able to sell at good profit. My wife always said that the money was f-in-law's and he could do what ever he wanted with it. But, b-in-law was always asking for money, the other siblings never did.
My father-in-law started having more health issues and needed someone to look after him so my sister-in-law kept him at home and took care of him. She realized that he would need to build him a separate room and larger bathroom. So she went to her brother and said to either build something or give the $$ back by selling the lot. He said it was worth less than he paid for it. They wonder if he even bought a lot, he probably spent it. He was able to build most of the spare room, but his sister got upset at him since he wasn't doing a good job and taking too long. So she got mad and did not have anything to do with him any more and had to finish the project with her own $$.
A year later b-in-law's DW came to us and sis-in-law and wanted $$ since things are slow or if we could buy their $1mill house for 650k, "it was a good deal" she said. We all said no we could not afford it (we are ER and do not want to risk our future!). She said they had drained their kids college $$ and retirement $$ just to make it. I heard later b-in-law was still spending like there's no tomorrow at the time.
His DW left him for someone else, now he is with his kids and he is living in a friends house for free since b-in-law lost his home since he took out a huge mortgage, $550k (probably spent it all).
F-in-law passed away and left life insurance $$ for all the siblings, no one is sure how much $$ so they are just waiting. It's probably not much. b-in-law claims to be at wits end and needs money. DW was thinking about giving her share the LI to him, but I said we would have to pay gift taxes on it. I said we could put in a bond fund and give him the interest. She agreed that he can't deal with $$. Probably shouldn't bail him out since he will just take on more risk and will never learn about living below his means. He's in a bad way since he's starting from scratch only a few years away from retirement age and 4 kids to put through college. Who knows if he's been contributing to SS since he's self employed. Only the one s-in-law is upset at him for basically squandering f-in-law $$ all those years and not helping out when it was needed. Everyone else seems to have forgotten about it but still not willing to help him with $$ since they have their own expenses to deal with. Being frugal, I think it's a shame that he squandered all the money. Oh well.
